5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]

Base Information

• Chemical Name: 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]
• CAS No.: 223387-28-8
• Molecular Formula: C₈₆H₇₄O₁₂
• Molecular Weight: 1299.53
• Mol file: 223387-28-8.mol

Synonyms:5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]

Chemical Property of 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]

Chemical Property:

• Density: 1.262±0.06 g/cm3(Predicted)

Purity/Quality:

5,7,3'',4''-Tetra-O-benzylepicatechin-4β→8-5,7,3'',4''-tetra-O-benzylepicatechin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5,7,3'',4''-Tetra-O-benzylepicatechin-4β→8-5,7,3'',4''-tetra-O-benzylepicatechin is an intermediate in the synthesis of Procyanidin B2 3,3''-Di-O-gallate (P755825). Procyanidin B2 3,3''-di-O-gallate is an important compound whose activity results in the inhibition of growth pertaining to human prostate carcinoma cell lines. Coming from the group of compounds known as flavonoids, Procyanidin B2 3,3''-di-O-gallate shows interesting biological activities relating to various human cancer diseases.

Technology Process of 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]

There total 14 articles about 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

5,7,3',4'-tetra-O-benzylepicatechin (87292-49-7) + 5,7,3',4'-tetra-O-benzyl-4β-(2-hydroxyethoxy)epicatechin (256236-25-6) → 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] (223387-28-8) + [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin (223387-30-2)

Guidance literature:

With Bentonite K-10; In dichloromethane; at 6 - 12 ℃; for 1h;

DOI:10.1021/jo020393f

Reference yield: 90.0%

[4,8']-2,3-cis-3,4-trans:2',3'-cis-octa-O-benzyl-3-O-acetyl-bi-(-)-epicatechin → 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] (223387-28-8)

Guidance literature:

With potassium carbonate; In methanol; at 60 ℃; for 12h;

DOI:10.3987/COM-08-S(D)14

Reference yield: 88.0%

bis(3-O-acetyl-5,7,3',4'-tetra-O-benzyl)epicatechin 4β,8-dimer (477565-90-5) → 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] (223387-28-8)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; Inert atmosphere;

DOI:10.1055/s-0035-1561390

upstream raw materials:

5,7,3',4'-tetra-O-benzylepicatechin

5,7,3',4'-tetra-O-benzyl-4β-(2-hydroxyethoxy)epicatechin

(2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol

benzyl bromide

Downstream raw materials:

procyanidin B₂-3,3'-di-O-gallate

5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin]

C₁₃₁H₁₁₂O₁₉

[4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin